当前位置： SCI文献检索 > BIOORGANIC & MEDICINAL CHEMISTRY期刊下所有文献 > Molecular design of N-linked tetravalent glycosides bearing N-acetylglucosamine, N,N'-diacetylchitobiose and N-acetyllactosamine: Analysis of cross-linking activities with WGA and ECA lectins.

Molecular design of N-linked tetravalent glycosides bearing N-acetylglucosamine, N,N'-diacetylchitobiose and N-acetyllactosamine: Analysis of cross-linking activities with WGA and ECA lectins.

Abstract：

:Two types of nonspacer- and spacer-N-linked tetravalent glycosides bearing N-acetylglucosamine (GlcNAc), N,N'-diacetylchitobiose [(GlcNAc)(2)] and N-acetyllactosamine (LacNAc) were designed and prepared as glycomimetics. The interactions of wheat germ (Triticum vulgaris) agglutinin (WGA) and coral tree (Erythrina cristagalli) agglutinin (ECA) with a series of tetravalent glycosides and related compounds were studied using a hemagglutination inhibition assay, a precipitation assay, double-diffusion test, and an optical biosensor based on surface plasmon resonance (SPR). The tetravalent glycosides were found to be capable of binding and precipitating the lectins as tetravalent ligands. Strong interactions with WGA, due to a combination of multivalency effects and spacer effects, were observed for tetravalent glycosides bearing flexible tandem GlcNAc. The chelate effect leads to large rate enhancement for the tetravalent system with favorable orientation of ligands. Our simple strategy produced multivalent glycosides with strong cross-linking activity for lectin as a specific coagulant.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Masaka R,Ogata M,Misawa Y,Yano M,Hashimoto C,Murata T,Kawagishi H,Usui T

doi

10.1016/j.bmc.2009.12.006

subject

Has Abstract

pub_date

2010-01-15 00:00:00

pages

621-9

issue

2

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(09)01089-X

journal_volume

18

pub_type

杂志文章

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